Pyrrolidinones and pyrrolidin thiones, and metal complexes thereof

Abstract

A compound of the general formula ##STR1## or a salt or complex thereof, in which X, Y and Z are all optionally substituted carbon atoms and R is hydrogen, optionally substituted hydrocarbyl or acyl or --COOR 7 and R 7 is hydrocarbyl has anti-microbial properties. Particular examples are compounds in which X is --CH 2 -- or --C(CH 3 ) 2 -- and Y and Z are both --CH 2 -- or X is is --CH 2 -- and Y and Z are carbon atoms of a benzene ring. The zinc complexes have useful properties.

We claim: 
     
       1. A compound of the formula ##STR7## wherein X 1  is a group --CR 1  R 2  -- or a group --CR 1  ═; Y 1  is a group --CR 3  R 4  -- or a group --CR 3  ═;   Z 1  is a group --CR 5  R 6  -- or a group --CR 5  ;   R is a hydrogen atom or an acyl group;   R 1  to R 6  are each, independently, a hydrogen atom or a methyl group; or R 1  and R 3  together with the carbon atoms to which they are attached, form a benzene ring, or R 3  and R 5 , together with the carbon atoms to which they are attached, form a -benzene ring; with the exception that   when X 1  is --C(CH 3 ) 2  --, R is --H or --CH 3  and Y 1  is --CH 2 , Z 1  is neither --CH 2  -- nor --C(CH 3 ) 2  --; and   when X 1  is --C(CH 3 ) 2  --, R is --H or --CH 3  and Z 1  is --CH 2  --, Y 1  is not --CH(CH) 3 .   
     
     
       2. The compound of claim 1 wherein X 1  is --CH 2  --. 
     
     
       3. A compound of the formula ##STR8## wherein X is a group --CR 1  R 2  -- or a group --CR 1  ═; Y is a group --CR 3  R 4  -- or a group --CR 3  ═;   Z is a group --CR 5  R 6  -- or a group --CR 5  ;   R is a hydrogen atom or an acyl group;   R 1  to R 6  are each, independently, a hydrogen atom or a methyl group; or R 1  and R 3  together with the carbon atoms to which they are attached, form a benzene ring, or R 3  and R 5 , together with the carbon atoms to which they are attached, form a benzene ring.   
     
     
       4. The salt or complex of claim 3 wherein X is --CH 2  --. 
     
     
       5. The salt or complex of claim 3 which is a complex with zinc. 
     
     
       6. 1-acetoxy-2-pyrrolidinthione; or 1-acetoxy-5,5-dimethyl-2-pyrrolidinthione. 
     
     
       7. A 2:1 2-hydroxy-2,3-dihydro-1H-isoindol-1-thione/zinc complex; a 2:1 1-hydroxy-2-pyrrolidinthione/zinc complex; or   a 2:1 5,5-dimethyl-1-hydroxy-2-pyrrolidinthione/zinc complex.